Don Draper

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Mad Men

This dashing, mysterious and incredibly talented '60s advertising executive has seemingly got the perfect life -- a beautiful wife, healthy kids and a stellar career. However, Don Draper's notorious womanizing and deep-seeded identity issues consistently threaten to ruin everything. Now, Draper's chronic infidelity alone isn't enough to make him our No. 1 TV jerk (after all, our list is peppered with cheaters). What does make him No. 1 is that, more than any other man on our list, he has such potential to be a good man.

In one sense, Draper is respectful toward women. In an era where women were openly objectified in the office, Draper refrained from this behavior, even lecturing the rakish Pete Campbell about this in the first episode. He recognized the talent in his bright secretary Peggy Olson and gave her a chance to become a copywriter.

However, he's continued his womanizing ways, even after his wife Betty took him back. And this makes Draper the cruelest offender of all: because he convinces you he can change, and you know how good a man he'd be if he did change. But, like Mad Men itself, it's just a case of history repeating itself.